Come to think of it, I used to worry more about ways to keep in touch. I customized my address book so that it would keep track of the last time I e-mailed or met someone and so that I could see whom I hadn’t contacted in a while. Some people are easy to connect with because you interact with them frequently or bump into them a lot online, but there are lots of other interesting people who don’t – and so you’d need to reach out to them in order to find out what’s going on.

After I stopped being able to use Emacs for my mail, I tried out different personal contact relationship management systems like Contactually and Nimble to see if I could have that kind of contact tracking there. It was pretty interesting, and sometimes I used the prompts to focus on one or two people I hadn’t heard from in ages. I checked their Facebook page or Twitter to see what they’ve been up to and looked for excuses to help them or reach out to them. Sometimes that led to interesting conversations.

I often deleted the reminders, though, and I decided it wasn’t worth paying something like $20/month for that kind of a reminder service. I’m becoming more comfortable with the way people flow into and out of one’s life. There are some old friends I get to talk to once in a while, which is wonderful, but I’m in no rush to develop old acquaintances into friendships.

There are lots of awesome people out there, so I can go with the flow – to respond to people, and to reach out when something prompts me. I’ve gotten pretty good at being open and comfortable with people. I remember what it’s like to be around close friends, and I get as close as I can to that as I can even with new groups. I don’t have the same kind of everyday camaraderie I had in my old circles of friends, but that makes sense in this part of my life. (Although Hacklab feels like an instant barkada too, with the way they’re friends with each other. ^_^ Hmm…)

So instead of worrying about keeping in touch, I keep part of my budget for coffee, lunches, dinners, tea parties, and stamps, spend time with friends in leisurely conversation or shared activities, and read people’s blogs and Facebook updates. I’m a little sad that it means my circles tend to be tilted towards people who are active on the Internet or who are in the same city as I am, and I know there are wonderful people whom I’m missing. But life moves in mysterious ways, so let’s see!

Eric and I were talking about the ways of making friends, and I wanted to reflect on it further. Here’s what I’ve learned so far!

Friendship is good, at least according to Aristotle and a whole bunch of other philosophers, psychologists, and researchers. Some people seem to develop friendships effortlessly. Others don’t particularly focus on it. W- says that I’m better at it than I think I am, but it’s useful for me to think of this as something in which I’m a relative beginner. That way, I can see the parts and learn more about how they fit together.

I like developing friendships because:

Other people are awesome and I’m glad that they exist. Spending time with good people makes me feel even happier about life.

Conversations, letters, questions, and ideas help me learn all sorts of things that I might not have come across myself.

Working with friends helps make bigger things happen.

Life has its zigs and zags, and it’s good to share the journey with people. We can be sounding boards and safety nets for each other.

What are some of the key actions or stages? Where do I do things well, and how can I make things even better?

Meeting new people: I meet lots of people through presentations, meetups, blog posts, social media, and introductions. Sometimes friends bring interesting people to my tea parties, too. It’s easy for me to bump into new people.

Getting to know people: Chatting with someone at a meetup is one thing. Continuing the conversation over e-mail or coffee is another. In between, there’s the first hook: Is this someone I’d like to get to know? What common interests can we start with?Will we have interesting and comfortable conversations? Blog posts and presentations are great shortcuts for this because people can easily identify common interests. (“I’m a visual thinker too!”) I tend to respond better to people who are confident and who share some of the things they’ve been learning about too. If it’s just the surface details (who you are and what do you do?), it can be hard to go from there. I try to focus on getting to know quirky or inspiring things about other people as a way of making it easier to follow up with them.

Bumping into people frequently: Meetups are great for this because I can get to know the regulars. If people blog or are active in social media, I can bump into them there and learn more about their interests.

Getting to know people one-on-one: Coffee, lunch, or Skype chats let me learn more about what makes people tick. I’ve gotten to the point of having a one-hour chat with someone without worrying too much about imposing or about wasting people’s time. It feels a little awkward sometimes, but I figure that will go away with practice. Scheduling these is much better now that my assistant handles the details. For remote friends, e-mails and letters tend to be a great fit.

More conversations: Did we click? More conversations/letters/etc. can help us bounce ideas around or find out what’s going on in people’s lives. Most people don’t post as frequently as I do, so if I want to find out what they’re thinking about, I have to ask them. I’m decent at this and tend to be the one to reach out. Sharing things about myself and asking questions are good ways to encourage other people to share parts of their life too.

Mixing with other friends: I really like mixing friends because I get to know other aspects of people – things we’d probably have never gotten around to talking about on our own. Besides, it means I don’t have to worry about carrying half the conversation. I can mostly ask questions and share the occasional story or two. I’d like to get into the habit of hosting tea parties every other month or every quarter. I’d also like to have a clique of close friends who are close friends with each other, but I’m not sure how to establish that without the built-in affiliations of college, company, or accommodations (like the way housemates often become good friends). Anyway!

One thing I’m working on is creating more space to spend with people or working towards their welfare. I prefer spending my weekends with W-, so I rarely make it out to weekend things. I keep Mondays, Wednesdays, and Fridays generally free of consulting, so I can schedule lunches or coffees then. Weekday evenings are the best for getting together with people whose schedules aren’t as flexible. Weekends are great for writing letters. I’d like to grow into a wonderfully thoughtful sort of person, and thoughtfulness requires thought and time.

I’m pretty comfortable where I am, socially. I’m no longer as worried about losing touch with my friends from the Philippines (yay Facebook and letters and blogging), and I have frequent non-work conversations with people here as well as around the world. I think it’ll be fascinating to get even better at deepening friendships, learning more about other people’s lives, and being there for people. I’ve got a long way yet to go, but there’s time enough for friends.

I’ve been thinking about friendship as one of those things that I want to deliberately get better at through practice and reflection. It seems strange to think about it that way. I’m used to over-thinking things, though. I like how thinking things through helps me see and understand, although I’m not sure how far I’ll get on my limited life experience.

Fortunately, other people have thought about friendship, and people have been doing so for thousands of years. (Well. Sort of. You know what I mean.) Cue philosophy, stage right.

Aristotle’s Nichomachean Ethics classifies friendships as friendships of pleasure, utility, or virtue. Other philosophers have discussed friendship in terms of mutual caring, intimacy through self-disclosure, and shared activity. Stanford has a neat summary.

I’d like to get better at building friendships of virtue. I generally wish good for everyone I meet, but friendship involves a specificity of goodwill. In other words, I hope a friend like Clair will have a wonderful life not just because I hope people will have wonderful lives, but because she’s super-awesome and I feel warm and fuzzy about a world that has people like her in it. (Happy birthday!)

I think life would be even more wonderful if I can discover this warm-and-fuzzy feeling about more people, and to know myself through them. I run into an increasingly familiar set of people in various meetups or on the Internet. People I meet tend to be awesome and easy to admire. Blogging and social media updates have this peculiar undirected self-disclosure thing going on, so I think conversation might be what I need to work on more. I might not be reaching out enough. Shared activities would be another big thing to work on.

My memory is too fuzzy to trust when it comes to people (or pretty much anything else, come to think of it), so I take notes. In The Spirit of Kaizen, Robert Maurer wrote about how he advised someone to take small steps by simply writing down compliments, then complimenting people to other people, then graduating to complimenting people directly. I can practise by writing down those compliments, taking notes on how awesome people are.

We tend to shy away from thinking about friendships and other interpersonal relationships, because it seems too analytical, clinical, even manipulative. If I can learn how to think about this while being me, though, I think that might be interesting.

I find that I quite enjoy slowing down and spending time with friends, bringing people together for conversation. I still stress out a little beforehand, but thinking of the people makes it easier to tidy things up and get things ready. Then it’s different; it’s like preparing and wrapping a gift.

It’s a pleasure to see friends becoming friends with each other, too. It makes conversations easier, and I learn more about people because I can see all these other aspects.

I’d like to give this sort of care to friends far away, and to new ones as well. David’s figured part of this out – he has good friendships around the world. There’s much to learn, but it’s good to do so.

In the end, the search for that feeling is the common thread through almost everything I’ve done. … We are none of us long in this life, and I think we all want to believe that when we have to run our last lap, we won’t have to run it alone. I think we all want friends to keep pace with, day after day, while we’re alive, so that we can be sure that someone will be out there, still running, when we’re not.

I want to enjoy and be inspired by great friendships through the decades. It’s easy to be insular, but if no man can really be an island (or at least be healthy doing so), I might at least be a peninsula. =)

Speaking of planning ahead, Trent (The Simple Dollar) has great advice on what to do at life’s crossroads. Living a frugal life and keeping expenses down means that we can take more risks, yay.

I’ve been talking to people about my project of becoming more social, getting better at connecting. It makes sense. I get to practise and pick up tips at the same time. =) Sometimes people say, “Sacha, aren’t you already pretty social? How big is your network, anyway?” But it’s not about that, and I think I’m starting to figure out what it’s about.

There are so many interesting people. W-, of course, is gosh-darn-awesome. And there are all these wonderful people I’ve gotten to know: my family, my barkada, my ninongs and ninangs, my friends in Canada who helped me get the hang of those first few winters, my friends at work and in various clubs, my friends through this blog and Twitter and all these other networks, and people I have yet to become good friends with. So the limiting factor isn’t the lack of people to develop friendships with, but my ability to do so.

What does it mean to be friends with someone? In the Nichomachean Ethics, where he devotes a book of fourteen chapters to the topic of friendship, Aristotle distinguishes between friendships of utility, friendships of pleasure, and friendships of good character. Of these, I’m interested in friendships of good character. In this kind of friendship, you appreciate the goodness of other people and they appreciate yours. You wish them good, and they wish you good as well.

But it is natural that such friendships should be infrequent; for such men are rare. Further, such friendship requires time and familiarity; as the proverb says, men cannot know each other till they have ‘eaten salt together’; nor can they admit each other to friendship or be friends till each has been found lovable and been trusted by each. Those who quickly show the marks of friendship to each other wish to be friends, but are not friends unless they both are lovable and know the fact; for a wish for friendship may arise quickly, but friendship does not.

And also:

Now there are three grounds on which people love; of the love of lifeless objects we do not use the word ‘friendship’; for it is not mutual love, nor is there a wishing of good to the other (for it would surely be ridiculous to wish wine well; if one wishes anything for it, it is that it may keep, so that one may have it oneself); but to a friend we say we ought to wish what is good for his sake. But to those who thus wish good we ascribe only goodwill, if the wish is not reciprocated; goodwill when it is reciprocal being friendship. Or must we add ‘when it is recognized’? For many people have goodwill to those whom they have not seen but judge to be good or useful; and one of these might return this feeling. These people seem to bear goodwill to each other; but how could one call them friends when they do not know their mutual feelings? To be friends, then, the must be mutually recognized as bearing goodwill and wishing well to each other for one of the aforesaid reasons.

That makes me think of several things. First, to wish good for other people, you should know them beneath the surface. It’s easy to say that I wish my friends to be happy, but knowing the specific things they consider pleasurable or good means I can share good experiences, find good gifts, or help people grow.

I’m probably an outlier in terms of writing and making it easy for people to get to know me through my interests. If I’m going to get to know other people, then I’m going to need to take the initiative and reach out, maybe slowly getting a sense of a person over time. I can get better at this by also, say, compiling notes on people’s expressed preferences. (Yes, I’m a geek.)

Second, friendship is reciprocal. I can feel goodwill towards many people, such as the people I’ve gotten to know through blogs. Some may even feel goodwill for me back, without my knowing. Friendship, I think, is when we both know it and that mutual understanding influences our actions.

I think that people are rather better at caring about me than I am at caring about them. This doesn’t mean I don’t care about other people as much. It means that I think other people are more thoughtful and are better at making a connection, and that there’s plenty of room for me to learn. Add to that the occasional asymmetry of knowledge and it can be a little awkward, but I’m getting better at getting past the awkward bit and just focusing on getting to know people more.

One of the things I’m particularly curious about is developing friendships online. When I listed people I might call if I needed a favour or I needed someone to talk to, I realized that there were some people I’ve never actually seen in person. I’d like to get even better at cultivating friendships online. From literature and other people’s examples, it’s clearly possible to develop deep connections beyond your geographic reach. With many of my friends outside Toronto – or infrequently met even in the same city – it’s something worth learning more about.

A lot of this is a matter of time: time to learn about people, time to share experiences, time to build trust, and so on. I can’t do much to speed things up. But it’s also equally a matter of attention – if I don’t invest that attention, then that time will pass without much effect.

Of course, reflecting on the Ethics, I need to be careful that people and friendship don’t become means. It’s not about checking off a little checkmark on my list of things to learn, or dissecting people and finding out what makes them tick, or chasing the pleasure of making someone’s day.

So that’s what I’m talking about when I say I want to get better at connecting or I want to be more social. It’s not about making sure I’ve “got my dance card filled”, or that I go out to at least one get-together each week, or even that I remember to host tea. I think it’s more about knowing people more so that I can appreciate their goodness and wish them good, and about building deeper connections.